3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

Base Information

Chemical Name:3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester
CAS No.:74084-36-9
Molecular Formula:C₂₄H₃₀N₄O₁₂
Molecular Weight:566.522
Hs Code.:

Synonyms:3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

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Chemical Property of 3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

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Technology Process of 3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

There total 4 articles about 3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: (3-bromo-2-pyridyloxy)-6-O-tert-butyldiphenylsilyl-2-azido-2-deoxy-β-D-galactopyranoside

: 108-24-7
acetic anhydride

: 74084-36-9
3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

Guidance literature:: N-benzyloxycarbonyl-L-serine methyl ester; (3-bromo-2-pyridyloxy)-6-O-tert-butyldiphenylsilyl-2-azido-2-deoxy-β-D-galactopyranoside; With dimethylformamide borontrifluoride; In dichloromethane; at -20 - 0 ℃; for 1.5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h;

acetic anhydride; With pyridine; In tetrahydrofuran; stereoselective reaction;
DOI:10.1021/acs.orglett.6b01263

Reference yield:

: (3-bromo-2-pyridyloxy) 2-azido-2-deoxy-β-D-galactopyranoside

: 74084-36-9
3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C

2.1: dimethylformamide borontrifluoride / dichloromethane / 1.5 h / -20 - 0 °C

2.2: 5 h

With 1H-imidazole; dimethylformamide borontrifluoride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.orglett.6b01263

Reference yield:

: 68733-27-7
3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl iodide

: 74084-36-9
3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / molecular sieve 4 Angstroem, tetraethylammonium chloride / acetonitrile / 1.) 30 min; 2.) 2 min, RT

2: 1.) 4 Angstroem molecular sieve, 2.) mercuric cyanide, mercuric chloride / 1.) 30 min, nitromethane; 2.) nitromethane, 12 h, 70 deg C

With 4 A molecular sieve; tetraethylammonium chloride; mercury(II) cyanide; mercury dichloride; In acetonitrile;
DOI:10.1016/S0008-6215(00)85142-3